Water → HCID 19423641, compound

HRID 743639Notes

Reaction equation

HRID 743639 reaction equation
[CH2:1]([O:3][CH:4]1[C:13](=[C:14]=[O:15])[N:12]([CH2:16][CH3:17])[C:11]2[N:10]=[C:9]3[CH:18]=[C:19](F)[C:20]([F:22])=[CH:21][C:8]3=[CH:7][C:6]=2[C:5]1=[O:24])[CH3:2].Cl.Cl.[CH3:27][N:28]([CH3:33])[CH:29]1[CH2:32][NH:31][CH2:30]1.[OH2:34]>>[CH3:27][N:28]([CH3:33])[CH:29]1[CH2:32][N:31]([C:19]2[C:20]([F:22])=[CH:21][C:8]3[C:9]([CH:18]=2)=[N:10][C:11]2[N:12]([CH2:16][CH3:17])[C:13](=[C:14]=[O:15])[CH:4]([O:3][CH2:1][CH3:2])[C:5](=[O:24])[C:6]=2[CH:7]=3)[CH2:30]1.[CH3:27][N:28]([CH3:33])[CH:29]1[CH2:32][N:31]([C:19]2[C:20]([F:22])=[CH:21][C:8]3[C:9]([CH:18]=2)=[N:10][C:11]2[N:12]([CH2:16][CH3:17])[CH:13]=[C:4]([C:4]([O:3][CH2:1][CH3:2])=[O:34])[C:5](=[O:24])[C:6]=2[CH:7]=3)[CH2:30]1

Participants

5

Reactant 3

HCID 962WaterHCID 22121220N,N-dimethylazetidin-3-amine dihydrochlorideHCID 86749832HCID 86749832, compound

Product 2

HCID 19423641HCID 19423641, compoundHCID 86749831HCID 86749831, compound

Conditions

Temperature
20 °C

Procedure

8-(3-Dimethylamino-1-azetidinyl)-3-ethoxy-carbonyl-1-ethyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine was prepared under the conditions described in Example 2, but starting with 1.7 g of 3-ethoxy-carbonyl-1-ethyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine, and 1.3 g of 3-(dimethyl- amino)azetidine dihydrochloride. After reaction, the reaction mixture, cooled to approximately 20° C., is poured into 50 cm3 of water and extracted with 3 times 100 cm3 of dichloromethane. The combined organic extracts are washed with 3 times 150 cm3 of water and dried over magnesium sulphate. After concentration to dryness under reduced pressure (20 kPa) at approximately 40° C. the residue is taken up with 50 cm3 of ethyl ether, filtered off and washed with twice 50 cm3 of the same solvent. 2 g of 8-(3-dimethylamino-1-azetidinyl)-3-ethoxycarbonyl-1-ethyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine are obtained in the form of a yellow solid, melting point 232° C., which is used without further purification for the subsequent steps.

Workup

  1. customAfter reaction
  2. extractionextracted with 3 times 100 cm3 of dichloromethane
  3. washThe combined organic extracts are washed with 3 times 150 cm3 of water
  4. dry with materialdried over magnesium sulphate
  5. concentrationAfter concentration to dryness under reduced pressure (20 kPa) at approximately 40° C. the residue
  6. filtrationfiltered off
  7. washwashed with twice 50 cm3 of the same solvent

Sources & evidence

ORD record
ord-83254f4580d84c3d883157c8e0b79584
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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